This invention relates to the separation of alkene mixtures. More particularly, mixtures of alkenes are separated by formation of complexes with a cuprous fluorinated acetylacetonate followed by separation of the complexes based on separation factors. The present invention is especially useful for separating mixtures of linear 1-alkenes, branched 1-alkenes, and linear and branched internal alkenes.
It is known that certain cuprous salts form complexes with olefins. U.S. Pat. No. 3,401,112 describes a process for separating hydrocarbon mixtures of differing degrees of unsaturation and isomeric unsaturated hydrocarbons using a cuprous salt of the formula CuXA where XA is the anion of an oxy-acid. U.S. Pat. Nos. 3,754,047 and 3,755,487 disclose the use of a cuprous salt for complexing ligands such as olefins, aromatics, acetylenes, CO and the like from a solvent containing high boiling aromatic compounds. Sorbent materials are cuprous salts of weakly basic acids, e.g., CuAlCl.sub.4, CuBF.sub.4, CuPF.sub.6 and CuOOCCF.sub.3. Inorganic Chemistry, 11, 2840 (1972) teaches the preparation of Ag(I) complexes containing hexafluoroacetylacetone and olefins. The preparation occurs in aqueous medium using soluble Ag(I) salts. U.S. Pat. No. 4,279,874 relates to a process for removing CO from a gas stream which comprises contacting the gas stream with an absorbent solution containing a Cu(I) halogenated acetylacetonate complex thereby removing CO as a CO-containing complex. U.S. Pat. No. 4,347,066 describes a process for removing CO and unsaturated hydrocarbons from gas streams using cuprous oxalate complexes.
In the area of separating olefin mixtures, U.S. Pat. No. 3,518,323 relates to a process for separating isobutylene from n-butylene mixtures by selectively dimerizing the isobutylenes using a supported nickel oxide catalyst. U.S. Pat. No. 3,531,539 discloses a process for separating isobutene from a feedstream containing n-butenes and other hydrocarbons by a selective separation process employing molecular sieves having a pore size of about 8.0 to 8.2 .ANG.. U.S. Pat. No. 4,242,530 describes the separation of an isoolefin from an n-olefin using a fixed bed acidic cation exchange resin by dimerizing the isoolefin. The catalyst is packed in a distillation column thereby providing vapor and liquid phase contact. U.S. Pat. No. 4,313,016 teaches a process for removing isobutene from C.sub.4 hydrocarbon streams by passing the streams through a cation exchange resin at 50.degree. to 80.degree. C. wherein isobutene is oligomerized and separated.